You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Darren Lamb

I am a former Buddhist monk, and I was looking for fun and exciting ways to teach the Dharma. I decided to write fictional stories that have a strong Buddhist influence yet are not in any way a “spiritual” book, or a self-help book. One of my earliest books is called Rebirth and is a Buddhist zombie tale. When I was trying to find a publisher or a literary agent to work with, no one would touch my work because it is different from the norm that is currently being published. They were afraid there wouldn’t be a market and were unwilling to take a chance on something different. Read more>>

Kestrel Montes

Going full-time as an independent business owner was, without a doubt, the scariest thing I’ve ever done. I used to say, “I’d never own a business! I want someone else to worry about where my paycheck comes Read more>>

Tara Zulfikar

I’m originally from Jakarta, Indonesia, and in 10th grade, I told my parents I wanted to be a filmmaker and study at NYU. They chuckled, assuming it was just a dream that would fade away. You can imagine their surprise when I was actually accepted to NYU’s Film & Television program. Suddenly, the questions started rolling in: Why film? Why so far from home? Really, film?! Read more>>

Atlanta Amado

I made my way to New York in a series of steps. I grew up on the Gulf of Mexico, in an idyllic little beach town + while it is absolute perfection in many ways, I knew I wouldn’t live there forever. My stops along the way were uni in Orlando, a few years at the beach in Miami, & Cairo Egypt (yes, that one) before I finally arrived in the city. Read more>>

Elstabo Artist

I participated in a group art show in Florida while working and living in New York. At that time, I was conflicted about attending the show, considering I didn’t have enough money to travel and take off from my day job. Days before the event, I was given a notice from my job that I was being terminated. So, feeling defiant, I booked the flight, car, and hotel room on my credit card with no backup resources to pay it off. I took the chance, reminding myself I would make the most of the trip and enjoy myself. The event was exciting and filled with art lovers of all kinds. That night, I met two college women who invited me for drinks. We ended up at a night club and partied till the next morning. Read more>>

Rebecca Anne Nguyen

I had no business writing a novel. As a writer, I had written everything but fiction: memoir, essays, all sorts of nonfiction, as well as theatrical works like stage plays and screenplays. But I’d never written so much as a short story. The real world interested me too much, and I felt like I wanted to tell real stories about real people, including myself. Read more>>

Gigi Kuhn

My biggest risk was to move from Paris to Chicago in 1998, knowing very little about Chicago, no internet, no social media, zero friend or family in America. It was a huge leap of faith from a school internship to a lifelong change to this day. 27 years later, I am still in Chicago, I never left. Read more>>

Melissa Poley

Risk-taking often gets a bad reputation, but for me, it’s actually about embracing my authentic self and aligning my actions with who I truly am. Whether it’s opening a business, navigating the difficult path of divorce, renting to people, or incorporating new ideas and services into my business, each decision might seem risky on the surface, but it’s a step toward being true to myself. These risks are not just about potential gains or losses; they’re about rediscovering my purpose and reclaiming the freedom to shape my life and my business the way I’ve always envisioned. Read more>>

Julian Llouve

I took immense risks to stay true to my vision as an illustrator, living as a nomad for years and traveling from city to city, never settling for easy compromises. Despite the uncertainty, I remained relentless in pursuing my own style, refusing to sell out to fleeting trends. Every sacrifice, every night spent in unfamiliar places, was a testament to my dedication—choosing artistic integrity over comfort, knowing that true success comes from never giving up on your vision. Read more>>

Travis Sprague

In 2013, after having a very fun time travelling around and playing metal music, I decided to step away from music altogether. I was newly married and being from the southern United States, playing metal in a band wasn’t exactly a financially stable career path. That, and being on the road away from my newly-wed wife, was not easy. I made a very great career out of retail management for a while and then decided to start plumbing, all the while, I still had the dream of being a professional musician. Read more>>

Laurie Kirby

As a lawyer in a large firm, I made an unconventional career pivot, leaving behind a stimulating and frankly lucrative career to follow my passion for film and film festivals in Newport, Rhode Island. Transitioning into the role of a festival director, I embraced the excitement and challenges of managing a large-scale regional destination film festival for the community at a tremendously reduced salary and with many unanticipated challenges to boot. Read more>>

Keesha Rivers

When I decided to step out on faith and move to California ( my dream state), it was definitely a process. It took so much to get here. I have a son and two grandsons , so I had to ask myself “ Is it worth it to move over 3,000 miles from everyone and everything you have ever known?” Read more>>

Marissa Ortiz

One of my most memorable moments in life where I took a risk was starting my own company, along with just starting my lifelong vision and journey of speaking. I had just lost my long-term corporate job due to the pandemic. I had hit my lowest point at that point, literally rock bottom. That’s when I took a leap of faith, promised myself I would never work for another company again, and started a business, born at the beginning of COVID. Today, I operate a six-figure company, a thriving nonprofit, and am an award winning author and speaker. This is only the beginning. Read more>>

Isabella Bernal

One of the biggest risks I took was leaving the stability of corporate life to dive into the world of startups. After gaining experience at respected companies like IBM, SAP, and Oracle, I had built a comfortable career path, one that many would consider a success.However, there was a pivotal moment when I took a brief detour into the startup world and worked for a startup that later became a unicorn and a startup founded by a Shark from Shark Tank. These experiences combined with the experience of mentoring startups from my SAP role ignited my curiosity to the fast-paced, high-stakes world of startups. Read more>>

Kay Harper

Ever since I was a little girl, I have been a musician at heart—a singer, a songwriter. For years it was a part of me that stayed in the background while I focused on life, responsibilities, and eventually raising my kids. I played shows here and there, I wrote songs, but I always treated it like a dream for someday—not something I was really allowed to truly chase. Read more>>

Rachel Wroblewski

One of the biggest risks I have taken was defiantly within the last year. I graduated with my master’s degree in Healthcare Administration and spent 2 years working at major hospital systems in my area. Unfortunately I had to take a leave to take care of my father who’s health had gone downhill. My mom passed away almost 6 years ago from ovarian cancer so it has just been him, the dog (Lila), and I. During this time of taking care of my father I realized that healthcare was not where my heart was, where my passion was. I do love and enjoy taking photos and being creative, that is my outlet. However, there is something else that my heart and passion’s desired and that was going to esthetician school. Read more>>

Kenneth Watson, Jr. Jd

I might have hesitated if you had told me years ago that I’d leave behind the security of my previous ventures to launch HealthLink360, an AI-driven health equity platform. But some risks aren’t just about business—they’re about purpose.

My journey into health innovation didn’t start in a boardroom. It started in kitchens, hospitals, and shelters. As the founder of Esquire Meals, I prepared hundreds of nutritious meals for wellness-focused individuals, cancer patients, and homeless shelters. I saw firsthand how access—or the lack thereof—impacted people’s ability to manage their health. Read more>>

Hannah Cherry

Before I became a yoga teacher, I was a body piercer for 11 years. I owned a successful business I had built for myself over the years. Unfortunately, standing all day for long hours and leaning over customers while piercing/changing their jewelry had taken such a toll on my back. I didn’t have any type of wellness/self-care practice, and my body was suffering. I remember nights where I would go home after work, take 5 ibuprofen and fall asleep on my heating pad. At one point, a yoga studio opened right below the tattoo shop I was working at. The owner came in to buy jewelry from me, and she was kind and inviting. I started taking some classes at her studio intermittently. Read more>>

Lara Hakamaki

Taking risks in business isn’t just about financial stakes—it’s about believing in something bigger than the fear of failure. At Michigan Psychological Care, we took a massive leap of faith when we decided to expand from three therapy offices to five, opening two new locations on the same day. It was a bold decision, one that stretched our resources, tested our resilience, and required immense dedication from our administrative team. Read more>>

Hallie Happy

I was told my entire life leading up to college, by people very close to me at that time in my life, that “You won’t make photography a career.” Naturally as a young girl around people who were so successful in their lives, I believed them. They had years of experience ahead of me. Some of them were even business owners, they knew what it took. I let many years go by where I told myself the exact same things those people told me. I wouldn’t make it a career. I wouldn’t make money. I needed to do something else with my life. I entered college, knowing it wasn’t right for me at that time, after a family member threatened to not help me with tuition if I didn’t go right out of high school. Wasted two years of college taking classes, switching majors constantly and just felt really lost. Read more>>

Teysha Wheeler-lemanski

I have always been bold, pushing boundaries, taking risks, and finding creative solutions to challenges. As a child battling autoimmune diseases, art and creativity became my refuge, a constant source of comfort and expression. That creative instinct has shaped my approach to life, fueling my passion for problem-solving in meaningful ways. Read more>>

Maryam Faison

I was always quiet growing up never really communicated with anyone like that, so I used art as my voice and to express whatever was going on in my head. So as I had gotten older I opened up more, and art became more challenging as the age of the internet became more accessible, everything was becoming more easier to learn and find, and that took a toll on me mentally because I wanted to learn how ideas were formed digitally, we hadn’t got internet til we were much older, so as I progressed into adulthood I started working with digital art and it was a learning experience for sure, if you messed up a piece you were creating you couldn’t just ball up a piece of paper nope you used a stylus, taking a risk was learning something new and I’ve been trying new techniques and experimenting with different methods of making my ideas come to life. Read more>>

Mickella Rumbolt

One of the biggest risks I’ve taken so far was starting my business, Chosen Designs. It had always been a dream of mine—a vision I held for years—but turning that dream into reality required taking a leap into the unknown. I didn’t have much experience in fashion or design, but I was incredibly passionate about it. I didn’t know the first thing about running a business Read more>>

Charla Adams

I have never been one to shy away from risk. Leaving the South to attend law school in Michigan was one of the biggest leaps of faith I’ve ever taken. It meant stepping into the unknown, facing new challenges, and proving to myself that I was capable of more than I ever imagined. Law school tested me in every way—long nights, moments of doubt, and the constant pressure to succeed. But quitting was never an option. Read more>>

Mona Amin

I remember staring at my laptop late at night, exhausted after another long day in corporate medicine. My husband and I were both doctors, drowning in student loans, and I felt stuck in a system that didn’t align with the impact I wanted to make. I loved caring for families, but the rigid structure of traditional medicine—rushed visits, burnout, and little autonomy—left me unfulfilled. Read more>>

Kelsey Lian

I decided to take a risk with high fashion modeling three years ago. Unfortunately, the fashion industry is notorious for putting people in specific ‘boxes’. The usual minimum height for female high fashion models is 5’9″. Standing at 5’6″, I’m automatically put into the petite category which fits into the commercial modeling ‘box’, more than high fashion. Although I do enjoy doing commercial modeling, it is not my main goal. My goal is to break the traditional barriers set in the fashion industry. I believe anyone can model and I want to help open up the high fashion industry to anyone. Looks can only take you so far, working hard and believing in yourself take you farther. This outlook is a risk in the fashion industry as I’m challenging what’s been the accepted norm for decades. Read more>>

William Perryman

One of the biggest risks I’ve taken recently would have to be starting the 52 in 52 song challenge this year. Basically, the challenge is you have to release 52 songs in 52 weeks. I’ve elected to drop a new song every Wednesday for the entire year. I’m dubbing them Wednesday with Will. Currently I’m 9 weeks into the year and I’ve released 9 songs with 3 of them being originals and 6 of them being remixes. So far I’ve released more music this year than I have in the past 3 years combined, which feels incredible and scary at the same time. Read more>>

Caitlyn Harris

The biggest risk I’ve ever taken was moving from a small town to a bigger city as a single mom to fully pursue my dreams as a hair and makeup artist. I made that decision 2 years ago knowing that would mean leaving behind an established clientele, steady and consistent income, and all around comfortable and stable lifestyle. Yet, I wanted more. I was in pursuit of something greater, and I knew this move would offer greater opportunity to explore my creative passions on a whole new level. Leaving behind the known for the unknown was an edgy move to make considering my circumstances, and I was willing to bet on myself and my skills that had already gotten me this far. This required immense courage and bravery to begin again and start building from scratch in a newer and much bigger environment. Read more>>

Matt Eskandari

One of the biggest risks I took was making my first feature film, “Victim” (2010). Fresh out of USC, I had no big studio backing—just a compelling but dark psychological thriller script and a drive to prove myself. Financing was tight, and I put everything I had into making it, pulling favors and stretching every dollar. Beyond the financial risk, the film’s unsettling themes were a creative gamble, but I refused to play it safe. Read more>>